Synthesis of Differentially Substituted 2-Aminoimidazolidines via a Microwave-Assisted Tandem Staudinger/Aza-Wittig Cyclization

Rakesh Kumar, Denis S. Ermolat'ev* and Erik V. Van der Eycken*

*Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, B-3001 Leuven, Belgium, Email: erik.vandereyckenchem.kuleuven.be, denis.ermolatevchem.kuleuven.be

R. Kumar, D. S. Ermolat'ev, E. V. Van der Eycken, J. Org. Chem., 2013, 78, 5737-5743.

DOI: 10.1021/jo400481b

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Abstract

The key step in a new route for the construction of 2-aminoimidazolidines is an intramolecular microwave-assisted Staudinger/aza-Wittig cyclization of an in situ generated urea intermediate upon treatment with Bu₃P or polymer-supported phosphine reagent. Furthermore, a useful one-pot Staudinger/aza-Wittig/Buchwald-Hartwig protocol leading to bicyclic guanidines has been elaborated.

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Key Words

imidazolines, microwave synthesis

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ID: J42-Y2013